US4234511A - Dialkylamino-N,N-bis(phosphonoalkylene)alkylamines and use in aqueous systems as precipitation and corrosion inhibitors - Google Patents
Dialkylamino-N,N-bis(phosphonoalkylene)alkylamines and use in aqueous systems as precipitation and corrosion inhibitors Download PDFInfo
- Publication number
- US4234511A US4234511A US06/061,168 US6116879A US4234511A US 4234511 A US4234511 A US 4234511A US 6116879 A US6116879 A US 6116879A US 4234511 A US4234511 A US 4234511A
- Authority
- US
- United States
- Prior art keywords
- bis
- phosphonoalkylene
- solution
- corrosion
- percent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/167—Phosphorus-containing compounds
- C23F11/1676—Phosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
- C02F5/14—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/3804—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se) not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3817—Acids containing the structure (RX)2P(=X)-alk-N...P (X = O, S, Se)
Abstract
Description
TABLE 1. ______________________________________ Inhibition of Calcium Carbonate Precipitation at pH 9. Con- cen- tration Parts PRODUCT TESTED per A B C D E F G H I Million PERCENT INHIBITION ______________________________________ 1.0 0 16.9 0 31.0 5.9 6.2 5.6 32.7 20.4 2.0 0 47.4 0 32.1 9.0 17.8 16.8 23.0 28.9 3.0 4.2 70.4 2.0 67.9 20.7 32.3 21.2 27.0 44.3 4.0 41.6 76.0 11.3 82.4 28.5 35.3 31.3 33.4 -- 5.0 50.9 82.4 47.1 87.2 30.1 49.5 28.0 44.4 26.4 6.0 54.5 90.2 0 88.3 41.0 55.6 34.0 48.8 22.1 7.0 64.1 90.5 4.5 93.1 50.4 65.2 33.2 50.4 57.0 8.0 60.6 92.9 25.6 94.8 52.0 69.6 35.3 56.8 82.1 9.0 69.4 93.2 28.7 95.9 57.4 77.7 47.9 52.5 77.0 10.0 67.5 93.6 36.9 92.4 60.0 78.6 43.8 55.4 87.7 Con- trol 2.05 2.05 1.21 1.45 1.21 0.71 0.89 0.89 2.98 Ca.sup.++ 6.14 6.14 6.09 4.35 6.09 6.00 5.71 5.71 5.33 blank ______________________________________
TABLE 2. __________________________________________________________________________ Corrosion Inhibition with the Compounds of this Invention Concen- CORROSION RATE tration Copper Inhi- Corrosion Parts per Initial Final Sump 1 Sump 2 Couple Average bition Inhibitor Million pH pH Miligrams per decimeter per day Percent __________________________________________________________________________ A 50 7.5 7.2 1.33 0.18 3.01 1.51 99.4 100 7.5 7.5 0.89 1.77 1.06 1.24 99.5 200 7.5 7.7 1.15 1.33 3.90 2.13 99.2 B 50 7.5 7.8 0.35 0.18 0.98 0.50 99.8 100 7.5 7.9 0.53 0.62 1.24 0.80 99.7 200 7.5 7.9 0.62 0.09 1.86 0.86 99.7 C 50 7.5 8.1 8.51 5.85 5.59 6.65 97.5 100 7.5 8.2 4.61 3.46 4.43 4.17 98.4 150 7.5 8.1 5.41 6.38 7.27 6.35 97.6 D 50 7.5 8.3 2.04 3.01 2.04 2.36 99.1 100 7.5 8.2 1.42 1.15 4.08 2.22 99.2 150 7.5 8.1 2.66 2.57 6.03 3.75 98.6 E 50 7.5 7.6 12.06 15.87 4.34 10.76 95.9 100 7.5 7.9 3.19 2.48 3.37 3.01 98.9 150 7.5 7.9 3.46 3.90 5.05 4.14 98.4 F 50 7.5 8.0 12.94 53.37 40.08 35.46 86.6 100 7.5 7.9 1.24 1.51 1.95 1.57 99.4 150 7.5 7.9 1.15 1.06 0.98 1.06 99.6 G 50 7.5 8.1 58.60 33.51 80.14 57.42 78.3 100 7.5 8.0 8.69 8.78 22.43 13.30 95.0 150 7.5 8.0 72.43 81.83 134.31 96.19 63.7 H 50 7.5 7.5 4.00 5.05 6.12 5.06 98.1 100 7.5 8.0 6.21 4.96 5.41 5.53 97.9 150 7.5 8.0 3.37 6.03 17.82 9.07 96.6 I 50 7.5 8.4 2.30 3.81 2.66 2.92 98.9 100 7.5 8.1 1.95 2.30 3.99 2.75 99.0 150 7.5 8.0 2.04 2.04 5.38 3.15 98.8 Control 0 7.5 7.8 193.0 258.0 356.0 269.0 0 Water Memphis Tap Water Temperature 50° C. Time Three days __________________________________________________________________________
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/061,168 US4234511A (en) | 1979-07-26 | 1979-07-26 | Dialkylamino-N,N-bis(phosphonoalkylene)alkylamines and use in aqueous systems as precipitation and corrosion inhibitors |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/061,168 US4234511A (en) | 1979-07-26 | 1979-07-26 | Dialkylamino-N,N-bis(phosphonoalkylene)alkylamines and use in aqueous systems as precipitation and corrosion inhibitors |
Publications (1)
Publication Number | Publication Date |
---|---|
US4234511A true US4234511A (en) | 1980-11-18 |
Family
ID=22034078
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/061,168 Expired - Lifetime US4234511A (en) | 1979-07-26 | 1979-07-26 | Dialkylamino-N,N-bis(phosphonoalkylene)alkylamines and use in aqueous systems as precipitation and corrosion inhibitors |
Country Status (1)
Country | Link |
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US (1) | US4234511A (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4459241A (en) * | 1983-04-28 | 1984-07-10 | The Dow Chemical Company | Compounds containing quaternary ammonium and methylenephosphonic acid groups |
US4493771A (en) * | 1983-04-28 | 1985-01-15 | The Dow Chemical Company | Scale inhibiting with compounds containing quaternary ammonium and methylenephosphonic acid groups |
US4857205A (en) * | 1988-02-22 | 1989-08-15 | Petrolite Corporation | Method for inhibition of scale formation |
US4931189A (en) * | 1988-11-02 | 1990-06-05 | Petrolite Corporation | Methods for inhibition of scale in high brine environments |
US5069798A (en) * | 1989-12-15 | 1991-12-03 | W. R. Grace & Co.-Conn. | Control of scale in aqueous systems using certain phosphonomethyl amines |
US5112496A (en) * | 1988-11-02 | 1992-05-12 | Petrolite Corporation | Methods for inhibition of scale in high brine environments |
US5181567A (en) * | 1990-05-23 | 1993-01-26 | Chevron Research And Technology Company | Method for prolonging the useful life of polymeric or blended scale inhibitors injected within a formation |
WO2008071689A2 (en) | 2006-12-11 | 2008-06-19 | Thermphos Trading Gmbh | Process for the manufacture of alkylamino alkylene phosphonic acids |
US20100123100A1 (en) * | 2008-11-20 | 2010-05-20 | Gill Jasbir S | Composition and method for controlling copper discharge and erosion of copper alloys in industrial systems |
US20110138683A1 (en) * | 2009-12-15 | 2011-06-16 | Instituto Mexicano Del Petroleo | Gemini surfactants, process of manufacture and use as multifunctional corrosion inhibitors |
WO2017096127A1 (en) | 2015-12-04 | 2017-06-08 | Ecolab Usa Inc. | Controlled release solid scale inhibitors |
US10865339B2 (en) | 2016-05-16 | 2020-12-15 | Championx Usa Inc. | Slow-release scale inhibiting compositions |
US11142680B2 (en) | 2016-12-23 | 2021-10-12 | Championx Usa Inc. | Controlled release solid scale inhibitors |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2599807A (en) * | 1950-06-01 | 1952-06-10 | Frederick C Bersworth | Alkylene polyamine methylene phosphonic acids |
US2841611A (en) * | 1954-09-01 | 1958-07-01 | Dow Chemical Co | Nu-alkyl substituted alkylene polyamine methylene phosphonic acids |
US2964549A (en) * | 1958-06-16 | 1960-12-13 | Victor Chemical Works | Alkanolaminealkanephosphonic acids and derivatives thereof |
US3160632A (en) * | 1961-01-30 | 1964-12-08 | Stauffer Chemical Co | Aminomethylenephosphinic acids, salts thereof, and process for their production |
US3288846A (en) * | 1961-11-13 | 1966-11-29 | Monsanto Co | Processes for preparing organophosphonic acids |
US4054598A (en) * | 1975-08-01 | 1977-10-18 | Henkel & Cie Gmbh | 1-Hydroxy-3-amino-alkane-1,1-diphosphonic acids and salts |
US4064164A (en) * | 1975-08-01 | 1977-12-20 | Henkel Kommanditgesellschaft Auf Aktien | 1,3-Di-amino-alkane-1,1-diphosphonic acids and salts |
-
1979
- 1979-07-26 US US06/061,168 patent/US4234511A/en not_active Expired - Lifetime
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2599807A (en) * | 1950-06-01 | 1952-06-10 | Frederick C Bersworth | Alkylene polyamine methylene phosphonic acids |
US2841611A (en) * | 1954-09-01 | 1958-07-01 | Dow Chemical Co | Nu-alkyl substituted alkylene polyamine methylene phosphonic acids |
US2964549A (en) * | 1958-06-16 | 1960-12-13 | Victor Chemical Works | Alkanolaminealkanephosphonic acids and derivatives thereof |
US3160632A (en) * | 1961-01-30 | 1964-12-08 | Stauffer Chemical Co | Aminomethylenephosphinic acids, salts thereof, and process for their production |
US3288846A (en) * | 1961-11-13 | 1966-11-29 | Monsanto Co | Processes for preparing organophosphonic acids |
US4054598A (en) * | 1975-08-01 | 1977-10-18 | Henkel & Cie Gmbh | 1-Hydroxy-3-amino-alkane-1,1-diphosphonic acids and salts |
US4064164A (en) * | 1975-08-01 | 1977-12-20 | Henkel Kommanditgesellschaft Auf Aktien | 1,3-Di-amino-alkane-1,1-diphosphonic acids and salts |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4459241A (en) * | 1983-04-28 | 1984-07-10 | The Dow Chemical Company | Compounds containing quaternary ammonium and methylenephosphonic acid groups |
US4493771A (en) * | 1983-04-28 | 1985-01-15 | The Dow Chemical Company | Scale inhibiting with compounds containing quaternary ammonium and methylenephosphonic acid groups |
EP0165333A1 (en) * | 1983-04-28 | 1985-12-27 | The Dow Chemical Company | New compounds containing quaternary ammonium and methylenephosphonic acid groups |
US4857205A (en) * | 1988-02-22 | 1989-08-15 | Petrolite Corporation | Method for inhibition of scale formation |
US4931189A (en) * | 1988-11-02 | 1990-06-05 | Petrolite Corporation | Methods for inhibition of scale in high brine environments |
US5112496A (en) * | 1988-11-02 | 1992-05-12 | Petrolite Corporation | Methods for inhibition of scale in high brine environments |
US5069798A (en) * | 1989-12-15 | 1991-12-03 | W. R. Grace & Co.-Conn. | Control of scale in aqueous systems using certain phosphonomethyl amines |
US5181567A (en) * | 1990-05-23 | 1993-01-26 | Chevron Research And Technology Company | Method for prolonging the useful life of polymeric or blended scale inhibitors injected within a formation |
WO2008071689A2 (en) | 2006-12-11 | 2008-06-19 | Thermphos Trading Gmbh | Process for the manufacture of alkylamino alkylene phosphonic acids |
US20100123100A1 (en) * | 2008-11-20 | 2010-05-20 | Gill Jasbir S | Composition and method for controlling copper discharge and erosion of copper alloys in industrial systems |
US8470238B2 (en) * | 2008-11-20 | 2013-06-25 | Nalco Company | Composition and method for controlling copper discharge and erosion of copper alloys in industrial systems |
US20110138683A1 (en) * | 2009-12-15 | 2011-06-16 | Instituto Mexicano Del Petroleo | Gemini surfactants, process of manufacture and use as multifunctional corrosion inhibitors |
DE102010053987A1 (en) | 2009-12-15 | 2011-07-07 | Instituto Mexicano Del Petroleo | New Gemini surfactants, manufacturing process and use as multifunctional corrosion inhibitors |
US8518868B2 (en) | 2009-12-15 | 2013-08-27 | Instituto Mexicano Del Petroleo | Gemini surfactants, process of manufacture and use as multifunctional corrosion inhibitors |
US9023785B2 (en) | 2009-12-15 | 2015-05-05 | Instituto Mexicano Del Petroleo | Gemini surfactants, process of manufacture and use as multifunctional corrosion inhibitors |
WO2017096127A1 (en) | 2015-12-04 | 2017-06-08 | Ecolab Usa Inc. | Controlled release solid scale inhibitors |
US10081758B2 (en) | 2015-12-04 | 2018-09-25 | Ecolab Usa Inc. | Controlled release solid scale inhibitors |
US10865339B2 (en) | 2016-05-16 | 2020-12-15 | Championx Usa Inc. | Slow-release scale inhibiting compositions |
US11142680B2 (en) | 2016-12-23 | 2021-10-12 | Championx Usa Inc. | Controlled release solid scale inhibitors |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: BUCKMAN LABORATORIES INTERNATIONAL, INC., 1256 NOR Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:BULAB HOLDINGS, INC.;REEL/FRAME:004772/0269 Effective date: 19871016 Owner name: BULAB HOLDINGS, INC. Free format text: CHANGE OF NAME;ASSIGNOR:BUCKMAN LABORATORIES, INC.,;REEL/FRAME:004800/0892 Effective date: 19870924 Owner name: BUCKMAN LABORATORIES INTERNATIONAL, INC.,TENNESSEE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:BULAB HOLDINGS, INC.;REEL/FRAME:004772/0269 Effective date: 19871016 Owner name: BULAB HOLDINGS, INC., DISTRICT OF COLUMBIA Free format text: CHANGE OF NAME;ASSIGNOR:BUCKMAN LABORATORIES, INC.,;REEL/FRAME:004800/0892 Effective date: 19870924 |